JP4079893B2 - 含フッ素環状化合物、含フッ素高分子化合物、それを用いたレジスト材料及びパターン形成方法 - Google Patents
含フッ素環状化合物、含フッ素高分子化合物、それを用いたレジスト材料及びパターン形成方法 Download PDFInfo
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- JP4079893B2 JP4079893B2 JP2004044142A JP2004044142A JP4079893B2 JP 4079893 B2 JP4079893 B2 JP 4079893B2 JP 2004044142 A JP2004044142 A JP 2004044142A JP 2004044142 A JP2004044142 A JP 2004044142A JP 4079893 B2 JP4079893 B2 JP 4079893B2
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- 229910052731 fluorine Inorganic materials 0.000 title claims description 143
- 239000011737 fluorine Substances 0.000 title claims description 127
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 title claims description 120
- 150000001875 compounds Chemical class 0.000 title claims description 109
- 229920000642 polymer Polymers 0.000 title claims description 83
- 239000000463 material Substances 0.000 title claims description 45
- 238000000034 method Methods 0.000 title claims description 33
- 150000001923 cyclic compounds Chemical class 0.000 title claims description 26
- -1 styrene compound Chemical class 0.000 claims description 100
- 239000000178 monomer Substances 0.000 claims description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims description 23
- 239000002253 acid Substances 0.000 claims description 21
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 16
- 150000001336 alkenes Chemical class 0.000 claims description 16
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 16
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Natural products C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 15
- 125000005843 halogen group Chemical group 0.000 claims description 13
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- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical compound [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- 238000000576 coating method Methods 0.000 claims description 6
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- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 5
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- URFLCXSTNZSALZ-UHFFFAOYSA-N [F].C(C(=C)C)(=O)O Chemical compound [F].C(C(=C)C)(=O)O URFLCXSTNZSALZ-UHFFFAOYSA-N 0.000 claims 7
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 claims 2
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- 238000006243 chemical reaction Methods 0.000 description 18
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 16
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- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 13
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- 238000003786 synthesis reaction Methods 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
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- 230000000704 physical effect Effects 0.000 description 7
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000007423 decrease Effects 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 6
- 229910052723 transition metal Inorganic materials 0.000 description 6
- 150000003624 transition metals Chemical class 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 238000005481 NMR spectroscopy Methods 0.000 description 5
- 238000000862 absorption spectrum Methods 0.000 description 5
- 125000004036 acetal group Chemical group 0.000 description 5
- 125000005234 alkyl aluminium group Chemical group 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 239000007789 gas Substances 0.000 description 5
- MUJIDPITZJWBSW-UHFFFAOYSA-N palladium(2+) Chemical compound [Pd+2] MUJIDPITZJWBSW-UHFFFAOYSA-N 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 5
- 229910052720 vanadium Inorganic materials 0.000 description 5
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 125000002252 acyl group Chemical group 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 238000004090 dissolution Methods 0.000 description 4
- WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 4
- 150000002221 fluorine Chemical class 0.000 description 4
- 239000003112 inhibitor Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000007870 radical polymerization initiator Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- WGTYBPLFGIVFAS-UHFFFAOYSA-M tetramethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)C WGTYBPLFGIVFAS-UHFFFAOYSA-M 0.000 description 4
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
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- 229910052782 aluminium Inorganic materials 0.000 description 3
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- NIMLCWCLVJRPFY-UHFFFAOYSA-N 1-(5-bicyclo[2.2.1]hept-2-enyl)ethanone Chemical compound C1C2C(C(=O)C)CC1C=C2 NIMLCWCLVJRPFY-UHFFFAOYSA-N 0.000 description 2
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 2
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- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 1
- 238000010538 cationic polymerization reaction Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- HYZXMVILOKSUKA-UHFFFAOYSA-K chloro(dimethyl)alumane;dichloro(methyl)alumane Chemical compound C[Al](C)Cl.C[Al](Cl)Cl HYZXMVILOKSUKA-UHFFFAOYSA-K 0.000 description 1
- 229940061627 chloromethyl methyl ether Drugs 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 229940125797 compound 12 Drugs 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000006841 cyclic skeleton Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical class 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- JAGHDVYKBYUAFD-UHFFFAOYSA-L cyclopenta-1,3-diene;titanium(4+);dichloride Chemical compound [Cl-].[Cl-].[Ti+4].C1C=CC=[C-]1.C1C=CC=[C-]1 JAGHDVYKBYUAFD-UHFFFAOYSA-L 0.000 description 1
- 125000000058 cyclopentadienyl group Chemical group C1(=CC=CC1)* 0.000 description 1
- QRUYYSPCOGSZGQ-UHFFFAOYSA-L cyclopentane;dichlorozirconium Chemical compound Cl[Zr]Cl.[CH]1[CH][CH][CH][CH]1.[CH]1[CH][CH][CH][CH]1 QRUYYSPCOGSZGQ-UHFFFAOYSA-L 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 1
- 150000004683 dihydrates Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- ZSWFCLXCOIISFI-UHFFFAOYSA-N endo-cyclopentadiene Natural products C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000003759 ester based solvent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- MGDOJPNDRJNJBK-UHFFFAOYSA-N ethylaluminum Chemical compound [Al].C[CH2] MGDOJPNDRJNJBK-UHFFFAOYSA-N 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- NJVOZLGKTAPUTQ-UHFFFAOYSA-M fentin chloride Chemical compound C=1C=CC=CC=1[Sn](C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 NJVOZLGKTAPUTQ-UHFFFAOYSA-M 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- ALDOUWLIYKWJTN-UHFFFAOYSA-N fluoro(dioxido)borane;nickel(2+) Chemical compound [Ni+2].[O-]B([O-])F ALDOUWLIYKWJTN-UHFFFAOYSA-N 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000017525 heat dissipation Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-M hexanoate Chemical compound CCCCCC([O-])=O FUZZWVXGSFPDMH-UHFFFAOYSA-M 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000007654 immersion Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 150000002484 inorganic compounds Chemical class 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 238000012690 ionic polymerization Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- AQBLLJNPHDIAPN-LNTINUHCSA-K iron(3+);(z)-4-oxopent-2-en-2-olate Chemical compound [Fe+3].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O AQBLLJNPHDIAPN-LNTINUHCSA-K 0.000 description 1
- LNOZJRCUHSPCDZ-UHFFFAOYSA-L iron(ii) acetate Chemical compound [Fe+2].CC([O-])=O.CC([O-])=O LNOZJRCUHSPCDZ-UHFFFAOYSA-L 0.000 description 1
- GYCHYNMREWYSKH-UHFFFAOYSA-L iron(ii) bromide Chemical compound [Fe+2].[Br-].[Br-] GYCHYNMREWYSKH-UHFFFAOYSA-L 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 239000005453 ketone based solvent Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- DCUFMVPCXCSVNP-UHFFFAOYSA-N methacrylic anhydride Chemical compound CC(=C)C(=O)OC(=O)C(C)=C DCUFMVPCXCSVNP-UHFFFAOYSA-N 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- CZRKJHRIILZWRC-UHFFFAOYSA-N methyl acetate;propane-1,2-diol Chemical compound COC(C)=O.CC(O)CO CZRKJHRIILZWRC-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- PDKHNCYLMVRIFV-UHFFFAOYSA-H molybdenum;hexachloride Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[Mo] PDKHNCYLMVRIFV-UHFFFAOYSA-H 0.000 description 1
- PZYDAVFRVJXFHS-UHFFFAOYSA-N n-cyclohexyl-2-pyrrolidone Chemical compound O=C1CCCN1C1CCCCC1 PZYDAVFRVJXFHS-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 1
- 229910000480 nickel oxide Inorganic materials 0.000 description 1
- UQPSGBZICXWIAG-UHFFFAOYSA-L nickel(2+);dibromide;trihydrate Chemical compound O.O.O.Br[Ni]Br UQPSGBZICXWIAG-UHFFFAOYSA-L 0.000 description 1
- AIYYMMQIMJOTBM-UHFFFAOYSA-L nickel(ii) acetate Chemical compound [Ni+2].CC([O-])=O.CC([O-])=O AIYYMMQIMJOTBM-UHFFFAOYSA-L 0.000 description 1
- 125000006502 nitrobenzyl group Chemical group 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical compound C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- GNRSAWUEBMWBQH-UHFFFAOYSA-N oxonickel Chemical compound [Ni]=O GNRSAWUEBMWBQH-UHFFFAOYSA-N 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- JKDRQYIYVJVOPF-FDGPNNRMSA-L palladium(ii) acetylacetonate Chemical compound [Pd+2].C\C([O-])=C\C(C)=O.C\C([O-])=C\C(C)=O JKDRQYIYVJVOPF-FDGPNNRMSA-L 0.000 description 1
- INIOZDBICVTGEO-UHFFFAOYSA-L palladium(ii) bromide Chemical compound Br[Pd]Br INIOZDBICVTGEO-UHFFFAOYSA-L 0.000 description 1
- HNNUTDROYPGBMR-UHFFFAOYSA-L palladium(ii) iodide Chemical compound [Pd+2].[I-].[I-] HNNUTDROYPGBMR-UHFFFAOYSA-L 0.000 description 1
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002120 photoresistant polymer Polymers 0.000 description 1
- 230000036211 photosensitivity Effects 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- QQZMDXUEROTLLD-UHFFFAOYSA-N rhodium;triphenylphosphane Chemical compound [Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QQZMDXUEROTLLD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000008054 signal transmission Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- AFCAKJKUYFLYFK-UHFFFAOYSA-N tetrabutyltin Chemical compound CCCC[Sn](CCCC)(CCCC)CCCC AFCAKJKUYFLYFK-UHFFFAOYSA-N 0.000 description 1
- YOUIDGQAIILFBW-UHFFFAOYSA-J tetrachlorotungsten Chemical compound Cl[W](Cl)(Cl)Cl YOUIDGQAIILFBW-UHFFFAOYSA-J 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- CRHIAMBJMSSNNM-UHFFFAOYSA-N tetraphenylstannane Chemical compound C1=CC=CC=C1[Sn](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 CRHIAMBJMSSNNM-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- FEONEKOZSGPOFN-UHFFFAOYSA-K tribromoiron Chemical compound Br[Fe](Br)Br FEONEKOZSGPOFN-UHFFFAOYSA-K 0.000 description 1
- 229910052905 tridymite Inorganic materials 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- LFXVBWRMVZPLFK-UHFFFAOYSA-N trioctylalumane Chemical compound CCCCCCCC[Al](CCCCCCCC)CCCCCCCC LFXVBWRMVZPLFK-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/40—Halogenated unsaturated alcohols
- C07C33/44—Halogenated unsaturated alcohols containing rings other than six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/34—Halogenated alcohols
- C07C31/44—Halogenated alcohols containing saturated rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/29—Saturated compounds containing keto groups bound to rings
- C07C49/337—Saturated compounds containing keto groups bound to rings containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/527—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings
- C07C49/573—Unsaturated compounds containing keto groups bound to rings other than six-membered aromatic rings containing hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/62—Halogen-containing esters
- C07C69/65—Halogen-containing esters of unsaturated acids
- C07C69/653—Acrylic acid esters; Methacrylic acid esters; Haloacrylic acid esters; Halomethacrylic acid esters
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F14/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a halogen
- C08F14/18—Monomers containing fluorine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Description
(8)に記載の化合物から誘導できる重合性の単量体である。フッ素原子を含有することによる効果、ヘキサフルオロイソプロパノール構造を有することによる効果、環状構造、特に多環式の骨格を有することによる効果は、上記一般式(1)又は(2)で示したものと同じである。すなわち、一般式(9)において、R2〜R7はこの化合物の性質を著しく損なわない限り特に限定されず、水素原子、ハロゲン原子、炭素数1〜25の直鎖状、分岐状もしくは環状のアルキル基である。R8はカルボニル基又はメチレン基、もしくは単結合である。
Mo系、W系触媒が挙げられ、特に、塩化チタン、塩化バナジウム、バナジウムトリスアセチルアセトナート、バナジウムビスアセチルアセトナートジクロリド、塩化モリブデン、塩化タングステンなどが好ましい。触媒量としては、使用モノマーに対して10mol%から0.001mol%、好ましくは、1mol%から0.01mol%である。
物性データ
化合物2
IR(cm-1): (異性体1,2の混合物):3294, 3069, 2979, 2947, 2877, 1697, 1448, 1273, 1240, 1198, 1164, 1149, 1099, 1033, 979, 709, 636
1H-NMR(TMS, CDCl3): (異性体1): 1.36(m, 1H), 1.52(m, 2H), 1.83(m, 1H), 2.94(q, 2H), 2.97(brs, 1H), 3.14(m, 1H), 3.28(brs, 1H), 5.84(dd,1H), 6.22(dd, 1H), 6.99(s, 1H),
(異性体2): 1.31(m, 1H), 1.52(m, 2H), 1.95(m, 1H), 2.97(brs, 1H), 3.00(brs, 1H), 3.06(brs, 1H), 3.14(m, 1H), 6.14(dd,1H), 6.22(dd, 1H), 7.05(s, 1H)
19F-NMR(CFCl3, CDCl3): (異性体1): -78.82(q, 3H), -78.63(q, 3H), (異性体2): -78.82(q, 3H), -78.63(q, 3H)
GC-MS(EI): (異性体1): m/e 302(M+), 237, 217, (異性体2): m/e 302(M+), 237, 217
物性データ
化合物3
IR(cm-1): (異性体1,2,3,4の混合物): 3425, 3068, 2979, 2933, 2908, 2868, 1314, 1281, 1225, 1202, 1166, 1151, 1140, 1052, 1042, 1004, 979, 719
1H-NMR(TMS, CDCl3): (異性体1): 0.52(m, 1H), 1.28-1.53(m, 2H), 1.83-2.39 (m, 5H), 2.60-2.99(m, 2H), 3.61(t, 1H), 6.01(dd, 1H), 6.22(s, 1H), 6.27(dd, 1H), (異性体2): 0.93(m, 1H), 1.28-1.53(m, 2H), 1.83-2.39 (m, 5H), 2.60-2.99(m, 2H), 3.71(t, 1H), 5.91(dd, 1H), 6.13(s, 1H), 6.27(dd, 1H), (異性体3): 0.52(m, 1H), 1.28-1.53(m, 2H), 1.83-2.39 (m, 5H), 2.60-2.99(m, 2H), 4.05(t, 1H), 6.11(dd, 1H), 6.27(s, 1H), 6.27(dd, 1H), (異性体4): 1.03(m, 1H), 1.28-1.53(m, 2H), 1.83-2.39 (m, 5H), 2.60-2.99(m, 2H), 3.95(t, 1H), 6.27(s, 1H), 6.27(m, 2H)
19F-NMR(CFCl3, CDCl3): (異性体1,2,3,4の混合物): -80.01(q, 3H), -76.08(q, 3H)
GC-MS(EI): (異性体1): m/e 304(M+), 286(-H2O), 267(-H2O,-F), 237, (異性体2): m/e 304(M+), 286(-H2O), 267(-H2O,-F), 237, (異性体3): m/e 304(M+), 286(-H2O), 267(-H2O,-F), 237, (異性体4): m/e 304(M+), 286(-H2O), 267(-H2O,-F), 237
物性データ
化合物5
IR(cm-1): (異性体1,2の混合物): 3301, 2960, 2877, 1696, 1455, 1367, 1322, 1273, 1238, 1194, 1163, 1027, 977, 719, 697, 651
1H-NMR(CDCl3): (異性体1): 1.10-1.70(m, 7H), 1.91(m, 1H), 2.35(t, 1H), 2.50(m, 2H), 2.91(d, 1H), 3.01(d, 1H), 7.07(s, 1H), (異性体2): 1.10-1.70(m, 7H), 1.73(m, 1H), 2.32(t, 1H), 2.65(t, 1H), 2.81(d, 1H), 2.95(m, 1H), 3.01(d, 1H), 7.06(s, 1H)
19F-NMR(CFCl3, CDCl3): (異性体1): -78.82(q, 3H), -78.65(q, 3H), (異性体2): -79.07(q, 3H), -78.49(q, 3H)
GC-MS(EI): (異性体1): m/e 304(M+), 286(-H2O), 263, 237, (異性体2): m/e 304(M+), 286(-H2O), 263, 237
物性データ
化合物6
IR(cm-1): (異性体1,2,3,4の混合物): 3448, 3093, 2958, 2915, 2867, 1457, 1281, 1227, 1204, 1162, 1152, 1138, 1051, 1019, 994, 930, 850, 716, 671
1H-NMR(CDCl3): (異性体1): 0.90-2.42(m, 14H), 3.89(t, 1H), 6.33(s, 1H), (異性体2): 0.90-2.42(m, 14H), 3.75(t, 1H), 6.33(s, 1H), (異性体3): 0.90-2.42(m, 14H), 4.00(t, 1H), 6.29(s, 1H), (異性体4): 0.90-2.42(m, 14H), 4.03(t, 1H), 6.44(s, 1H)
19F-NMR(CFCl3, CDCl3): (異性体1): -79.98(q, 3H), -76.08(q, 3H), (異性体2): -80.00(q, 3H), -75.99(q, 3H), (異性体3): -80.00(q, 3H), -76.02(q, 3H), (異性体4): -79.93(q, 3H), -75.99(q, 3H)
GC-MS(EI): (異性体1): m/e 306(M+), 288(-H2O), 260, 237), (異性体2): m/e 306(M+), 288(-H2O), 260, 237, (異性体3): m/e 306(M+), 305, 288(-H2O), 260, 237, (異性体4): m/e 306(M+), 304, 288(-H2O), 259, 246
物性データ
化合物7
IR(cm-1): (異性体1,2,3,4の混合物): 3301, 2955, 2874, 1688, 2634, 1455, 1203, 1171, 1143, 1050, 1022, 1009, 946, 815, 715, 660
1H-NMR(CDCl3): (異性体1): 0.75-1.55(m, 8H), 1.75(m, 1H), 1.95(t, 3H), 2.09-2.45(m, 4H), 4.91(m, 1H), 5.67(m, 1H), 6.18(m, 1H), 6.21(s, 1H), (異性体2): 0.75-1.55(m, 8H), 1.75(m, 1H), 1.97(t, 3H), 2.09-2.45(m, 4H), 4.82(m, 1H), 5.57(s, 1H), 5.67(m, 1H), 6.18(m, 1H), (異性体3): 0.75-1.55(m, 8H), 1.75(m, 1H), 1.96(t, 3H), 2.09-2.45(m, 4H), 4.98(m, 1H), 5.67(m, 1H), 6.05(s, 1H), 6.18(m, 1H), (異性体4): 0.75-1.55(m, 8H), 1.75(m, 1H), 1.96(t, 3H), 2.09-2.45(m, 4H), 5.11(m, 1H), 5.67(m, 1H), 5.80(s, 1H), 6.18(m, 1H)
19F-NMR(CFCl3, CDCl3): (異性体1): -79.29(q, 3H), -77.00(q, 3H), (異性体2): -79.09(q, 3H), -77.14(q, 3H), (異性体3): -79.00(q, 3H), -77.34(q, 3H), (異性体4): -79.09(q, 3H), -77.65(q, 3H)
GC-MS(EI): (異性体1): m/e 374(M+), 359, 314, 305(-CF3), 288, (異性体2): m/e 374(M+), 359, 333, 316, 305(-CF3), (異性体3): m/e 374(M+), 356(-H2O), 305(-CF3), 288, (異性体4): m/e 374(M+), 356(-H2O), 305(-CF3), 288
Claims (21)
- 下記の一般式(3)で表される含フッ素環状化合物。
- 下記の一般式(4)で表される含フッ素環状化合物。
- 下記の一般式(5)で表される含フッ素環状化合物。
- 下記の一般式(6)で表される含フッ素環状化合物。
- 下記の一般式(7)で表される含フッ素環状化合物。
- 下記の一般式(8)で表される含フッ素環状化合物。
- 下記の一般式(9)で表される含フッ素環状化合物。
- 下記の一般式(10)で表される繰り返し単位からなり、または下記の一般式(10)で表される繰り返し単位と無水マレイン酸、アクリル酸エステル、含フッ素アクリル酸エステル、メタクリル酸エステル、含フッ素メタクリル酸エステル、スチレン系化合物、含フッ素スチレン系化合物、ビニルエーテル、含フッ素ビニルエーテル、アリルエーテル、含フッ素アリルエーテル、オレフィン、含フッ素オレフィン、ノルボルネン化合物、含フッ素ノルボルネン化合物、二酸化硫黄、ビニルシランから選ばれた一種類以上の単量体に由来する繰り返し単位を含むことを特徴とする重量平均分子量1,000〜1,000,000の含フッ素高分子化合物。
- 下記の一般式(11)で表される繰り返し単位からなり、または下記の一般式(11)で表される繰り返し単位と無水マレイン酸、アクリル酸エステル、含フッ素アクリル酸エステル、メタクリル酸エステル、含フッ素メタクリル酸エステル、スチレン系化合物、含フッ素スチレン系化合物、ビニルエーテル、含フッ素ビニルエーテル、アリルエーテル、含フッ素アリルエーテル、オレフィン、含フッ素オレフィン、ノルボルネン化合物、含フッ素ノルボルネン化合物、二酸化硫黄、ビニルシランから選ばれた一種類以上の単量体に由来する繰り返し単位を含むことを特徴とする重量平均分子量1,000〜1,000,000の含フッ素高分子化合物。
- 下記の一般式(12)で表される繰り返し単位からなり、または下記の一般式(12)で表される繰り返し単位と無水マレイン酸、アクリル酸エステル、含フッ素アクリル酸エステル、メタクリル酸エステル、含フッ素メタクリル酸エステル、スチレン系化合物、含フッ素スチレン系化合物、ビニルエーテル、含フッ素ビニルエーテル、アリルエーテル、含フッ素アリルエーテル、オレフィン、含フッ素オレフィン、ノルボルネン化合物、含フッ素ノルボルネン化合物、二酸化硫黄、ビニルシランから選ばれた一種類以上の単量体に由来する繰り返し単位を含むことを特徴とする重量平均分子量1,000〜1,000,000の含フッ素高分子化合物。
- 下記の一般式(13)で表される繰り返し単位からなり、または下記の一般式(13)で表される繰り返し単位と無水マレイン酸、アクリル酸エステル、含フッ素アクリル酸エステル、メタクリル酸エステル、含フッ素メタクリル酸エステル、スチレン系化合物、含フッ素スチレン系化合物、ビニルエーテル、含フッ素ビニルエーテル、アリルエーテル、含フッ素アリルエーテル、オレフィン、含フッ素オレフィン、ノルボルネン化合物、含フッ素ノルボルネン化合物、二酸化硫黄、ビニルシランから選ばれた一種類以上の単量体に由来する繰り返し単位を含むことを特徴とする重量平均分子量1,000〜1,000,000の含フッ素高分子化合物。
- 下記の一般式(14)で表される繰り返し単位からなり、または下記の一般式(14)で表される繰り返し単位と無水マレイン酸、アクリル酸エステル、含フッ素アクリル酸エステル、メタクリル酸エステル、含フッ素メタクリル酸エステル、スチレン系化合物、含フッ素スチレン系化合物、ビニルエーテル、含フッ素ビニルエーテル、アリルエーテル、含フッ素アリルエーテル、オレフィン、含フッ素オレフィン、ノルボルネン化合物、含フッ素ノルボルネン化合物、二酸化硫黄、ビニルシランから選ばれた一種類以上の単量体に由来する繰り返し単位を含むことを特徴とする重量平均分子量1,000〜1,000,000の含フッ素高分子化合物。
- 下記の一般式(15)で表される繰り返し単位からなり、または下記の一般式(15)で表される繰り返し単位と無水マレイン酸、アクリル酸エステル、含フッ素アクリル酸エステル、メタクリル酸エステル、含フッ素メタクリル酸エステル、スチレン系化合物、含フッ素スチレン系化合物、ビニルエーテル、含フッ素ビニルエーテル、アリルエーテル、含フッ素アリルエーテル、オレフィン、含フッ素オレフィン、ノルボルネン化合物、含フッ素ノルボルネン化合物、二酸化硫黄、ビニルシランから選ばれた一種類以上の単量体に由来する繰り返し単位を含むことを特徴とする重量平均分子量1,000〜1,000,000の含フッ素高分子化合物。
- 下記の一般式(16)で表される繰り返し単位からなり、または下記の一般式(16)で表される繰り返し単位と無水マレイン酸、アクリル酸エステル、含フッ素アクリル酸エステル、メタクリル酸エステル、含フッ素メタクリル酸エステル、スチレン系化合物、含フッ素スチレン系化合物、ビニルエーテル、含フッ素ビニルエーテル、アリルエーテル、含フッ素アリルエーテル、オレフィン、含フッ素オレフィン、ノルボルネン化合物、含フッ素ノルボルネン化合物、二酸化硫黄、ビニルシランから選ばれた一種類以上の単量体に由来する繰り返し単位を含むことを特徴とする重量平均分子量1,000〜1,000,000の含フッ素高分子化合物。
- 下記の一般式(17)で表される繰り返し単位を含むことを特徴とする請求項11〜14のいずれか1項に記載の重量平均分子量1,000〜1,000,000の含フッ素高分子化合物。
- 酸不安定性基を有した繰り返し単位を含むことを特徴とする請求項8〜15のいずれか1項に記載の含フッ素高分子化合物。
- 分子内に含まれる水酸基の一部又は全部が保護基によって保護されていることを特徴とする請求項1〜16のいずれか1項に記載の含フッ素環状化合物又は含フッ素高分子化合物。
- 請求項8〜17のいずれか1項に記載の含フッ素高分子化合物を含むことを特徴とするレジスト材料。
- 請求項18に記載のレジスト材料と光酸発生剤を含むことを特徴とする化学増幅型レジスト材料。
- 請求項18又は19に記載のレジスト材料を基板上に塗布する工程と、次に基板を熱処理する工程と、300nm以下の波長の高エネルギー線又は電子線を用いてフォトマスクを通して露光する工程と、露光されたレジストの塗布膜に対して熱処理を施す工程と、現像処理を施す工程を少なくとも含むことを特徴とするパターン形成方法。
- 用いる高エネルギー線がF2エキシマレーザー、ArFエキシマレーザー、KrFエキシマレーザー又は軟X線であることを特徴とする請求項22記載のパターン形成方法。
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US10/589,807 US7736835B2 (en) | 2004-02-20 | 2005-02-17 | Fluorine-containing cyclic compound, fluorine-containing polymer compound, resist material using same and method for forming pattern |
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TW094104884A TW200602301A (en) | 2004-02-20 | 2005-02-18 | Fluorine-containing cyclic compound, fluorine-containing polymer compound, resist material using same and method for forming pattern |
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JP3999030B2 (ja) * | 2001-12-13 | 2007-10-31 | セントラル硝子株式会社 | 含フッ素重合性単量体およびそれを用いた高分子化合物、反射防止膜材料 |
KR100486245B1 (ko) * | 2001-12-19 | 2005-05-03 | 삼성전자주식회사 | 하이드레이트 구조를 가지는 플루오르 함유 감광성 폴리머및 이를 포함하는 레지스트 조성물 |
JP4073337B2 (ja) | 2002-02-26 | 2008-04-09 | 富士フイルム株式会社 | 感光性樹脂組成物 |
US6806026B2 (en) * | 2002-05-31 | 2004-10-19 | International Business Machines Corporation | Photoresist composition |
JP4073253B2 (ja) | 2002-05-31 | 2008-04-09 | 富士フイルム株式会社 | ポジ型レジスト組成物 |
KR100740803B1 (ko) * | 2002-11-05 | 2007-07-19 | 샌트랄 글래스 컴퍼니 리미티드 | 불소가 함유된 비닐 에테르 및 이들의 중합체와 상기중합체를 이용한 레지스트 조성물 |
US7067691B2 (en) * | 2003-12-26 | 2006-06-27 | Central Glass Co., Ltd. | Process for producing α-substituted acrylic acid esters |
US7205443B2 (en) * | 2004-01-27 | 2007-04-17 | Central Glass Company, Limited | Processes for producing fluorine-containing 2,4-diols and their derivatives |
JP4484603B2 (ja) * | 2004-03-31 | 2010-06-16 | セントラル硝子株式会社 | トップコート組成物 |
US7385091B2 (en) * | 2005-08-03 | 2008-06-10 | Central Glass Co., Ltd. | Process for producing fluorine-containing diol and its derivatives |
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2004
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2005
- 2005-02-17 KR KR1020067017600A patent/KR100849126B1/ko not_active IP Right Cessation
- 2005-02-17 WO PCT/JP2005/002400 patent/WO2005080306A1/ja active Application Filing
- 2005-02-17 US US10/589,807 patent/US7736835B2/en not_active Expired - Fee Related
- 2005-02-18 TW TW094104884A patent/TW200602301A/zh not_active IP Right Cessation
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Also Published As
Publication number | Publication date |
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US20080003517A1 (en) | 2008-01-03 |
US8115036B2 (en) | 2012-02-14 |
TW200602301A (en) | 2006-01-16 |
KR100849126B1 (ko) | 2008-07-30 |
WO2005080306A1 (ja) | 2005-09-01 |
US7736835B2 (en) | 2010-06-15 |
US20100204422A1 (en) | 2010-08-12 |
KR20060117361A (ko) | 2006-11-16 |
TWI309640B (ja) | 2009-05-11 |
JP2005232095A (ja) | 2005-09-02 |
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